(-)-2-ethylapoisopinocampheol | 116951-41-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-2-ethylapoisopinocampheol
• 英文别名: (1R,2R,3R,5S)-2-ethyl-6,6-dimethylbicyclo[3.1.1]heptan-3-ol
• CAS: 116951-41-8
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: NBLGXAYJERSKHE-SGIHWFKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1S,5S)-2-ethyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene 生成 (-)-2-ethylapoisopinocampheol
  参考文献：
  名称：

  Brown Herbert C., Dhokte Ulhas P., J. Org. Chem., 59 (1994) N 9, S 2365- 2369

  摘要：

  DOI：

文献信息

• Hydroboration. 83. Synthesis and hydroboration of 2-ethylapopinene. Comparison of monoisopinocampheylborane and its 2-ethyl analog for the chiral hydroboration of representative alkenes
  作者：Herbert C. Brown、Ramnarayan S. Randad、Krishna S. Bhat、Marek Zaidlewicz、Steven A. Weissman、Prabhakar K. Jadhav、P. T. Perumal

  DOI：10.1021/jo00258a021

  日期：1988.11
• Hydroboration. 91. Improved Procedure for the Synthesis of Optically Pure Bis-adducts,N,N,N,'N'-Tetramethylethylenediamine.cntdot.2-organylapoisopinocampheylboranes, from the Corresponding 2-Organylapopinenes of Lower Optical Purity. Conversion of These Adducts into 2-Organylapoisopinocampheylboranes, Useful Asymmetric Hydroborating Reagents
  作者：Herbert C. Brown、Ulhas P. Dhokte

  DOI：10.1021/jo00088a016

  日期：1994.5

  The higher analogues of alpha-pinene, such as 2-ethyl-, 2-n-propyl-, 8-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes, were treated with borane-methyl sulfide (BMS) in the stoichiometry of 1.2:1, respectively, in anhydrous tetrahydrofuran (THF) at 25 degrees C, obtaining an equilibrium mixture of 2-organylapoisopinocampheylboranes (2-R-apoisopinylborane, RapBH(2)) as major and bis(2-organylapoisopinocampheyl)borane [bis(2-R-apoisopinyl)borane, Rap(2)BH] as minor constituents. Treatment of the equilibrium mixture of boranes with tetramethylethylenediamine (TMEDA) at 34 degrees C readily and selectively provided the optically pure bis(2-organylapoisopinocampheylborane) T adducts, (RapBH(2))(2).TMEDA, in satisfactory yield. This reaction is quite general and appears to be broadly applicable to the conversion of the sterically bulkier 2-organylapopinenes (2-R-apopinenes) with widely varied steric requirements and lower optical purity (87-92% ee) into the corresponding optically pure (RapBH(2))(2).TMEDA derivatives, approaching greater than or equal to 99% ee. Treatment of the crystalline bis-adduct in ethyl ether with BF3.EE precipitates (BF3)(2).TMEDA and provides RapBH(2) of essentially greater than or equal to 99% ee, enantiomerically purer than the 2-R-apopinenes of 87-92% ee utilized for these preparations.